title: Spontaneous formation of immunogenic conjugates by a biotransformation product of sulfanilamide.
abstract: 3-hydroxy-sulfanilamide (3-HS) has been previously shown to be formed in significant amounts in rabbits and humans treated with sulfanilamide. In the present paper we demonstrate that 3-HS reacts readily with proteins at alkaline pH and forms conjugates capable to induce hapten specific antibodies in rabbits. According to our previous observations on ortho-aminophenol (OAP), the haptenic properties of 3-HS are apparently due to the presence in its molecule of an ortho-aminophenolic structure, rendering it capable to form a highly reactive quinoneimine derivative. In spite of a similar mechanism of linking and of the presence of an ortho-aminophenolic structure in the two haptens, 3-HS and OAP immunological systems do not cross react with each other. The data presented here support the hypothesis that 3-HS may represent the hapten or one of the haptens involved in sulfonamide allergy.
mesh_terms: D000818:Animals; D000906:Antibodies / Q000032:analysis; D000917:Antibody Formation; D000918:Antibody Specificity; D001583:Benzoxazoles / Q000138:chemical synthesis; D001711:Biotransformation; D001798:Blood Proteins / Q000276:immunology; D011817:Rabbits / Q000276:immunology; D013424:Sulfanilamides / Q000138:chemical synthesis / Q000276:immunology*
chemical_list: D000906:Antibodies; D001583:Benzoxazoles; D001798:Blood Proteins; D013424:Sulfanilamides; C032870:3-hydroxysulfanilamide; C017057:benzoxazolone